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Issue 41, 2013
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Azobenzene-functionalized N-heterocyclic carbenes as photochromic ligands in silver(I) and gold(I) complexes

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Abstract

The reaction of meta- and para-bromomethylene-azobenzenes with 1-methyl-imidazole yields the respective meta-/para-functionalized azobenzenes tagged with an imidazolium group. Similar reactions of ortho- and para-bromo-azobenzene with imidazole and successive quaternation with benzylbromide give the analogues, with an imidazolium group in ortho/para substituted azobenzenes. With the exception of the ortho derivative, all imidazolium salts could be transformed into their respective silver(I) complexes by reaction with Ag2O. Transmetallation of these silver(I) complexes with (Me2S)AuCl gives the azobenzene-containing complexes (NHC)AuCl. Two of these formed crystals suitable for X-ray diffraction, which revealed the typical linear coordination geometry of the NHC–Au–Cl moiety. All gold complexes feature EZ photo-isomerisation upon irradiation with UV light. The thermal back reaction to the E-isomers is relatively slow and comparable to that of other azobenzene compounds.

Graphical abstract: Azobenzene-functionalized N-heterocyclic carbenes as photochromic ligands in silver(i) and gold(i) complexes

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Publication details

The article was received on 13 Jun 2013, accepted on 19 Jul 2013 and first published on 22 Jul 2013


Article type: Paper
DOI: 10.1039/C3DT51565F
Citation: Dalton Trans., 2013,42, 14749-14756
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    Azobenzene-functionalized N-heterocyclic carbenes as photochromic ligands in silver(I) and gold(I) complexes

    M. Kaiser, S. P. Leitner, C. Hirtenlehner, M. List, A. Gerisch and U. Monkowius, Dalton Trans., 2013, 42, 14749
    DOI: 10.1039/C3DT51565F

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